5543-27-1

Usage

Uses

Used in Recreational Substances:
4-BMC is utilized as a recreational substance for its capacity to produce euphoric and energizing effects. Its appeal lies in its ability to mimic the stimulating properties of traditional stimulants, making it a sought-after option for those seeking a temporary boost in mood and energy levels.
Used in Research Chemicals:
As a research chemical, 4-BMC is employed in scientific studies to explore its psychoactive properties and potential applications in various fields. (4-Bromophenyl)(pyrrolidin-1-yl)methanone's effects on the central nervous system make it a subject of interest for researchers investigating the mechanisms of action and potential therapeutic uses of similar stimulant substances.
Used in Pharmaceutical Development:
Although not yet a recognized pharmaceutical, 4-BMC's properties may inspire the development of new medications. Its stimulant effects could potentially be harnessed in controlled environments for the treatment of certain conditions, provided that the risks of addiction and side effects are mitigated through careful formulation and regulation.

InChI:InChI=1/C11H12BrNO/c12-10-5-3-9(4-6-10)11(14)13-7-1-2-8-13/h3-6H,1-2,7-8H2

Upstream product

• 123-75-1 pyrrolidine 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-75-4 4-chlorobenzoyl chloride 
• 586-76-5 4-Bromobenzoic acid 
• 201230-82-2 carbon monoxide 
• 5467-74-3 4-Bromophenylboronic acid 
• 4254-18-6 1,2-bis(4-bromophenyl)-2-hydroxyethan-1-one 
• 1380243-00-4 3-(4-bromobenzoyl) oxazolidin-2-one 
• 35578-47-3 4,4'-dibromobenzil 
• 39229-12-4 4-bromobenzil 
• 873-75-6 4-bromobenzenemethanol 
• 106-38-7 para-bromotoluene 

Downstream Products

• 1187051-98-4 (4-bromo-2-(3-methylbut-2-enyl)phenyl)(pyrrolidin-1-yl)methanone 
• 1073353-55-5 pyrrolidin-1-yl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone 
• 882689-88-5 (4-bromo-2-fluorophenyl)(pyrrolidin-1-yl)methanone 
• 276678-35-4 (4-bromo-2-methylphenyl)(pyrrolidin-1-yl)methanone 
• 4897-55-6 N-(p-bromobenzyl)pyrrolidine 
• 7295-44-5 4'-bromovalerophenone 
• 4160-65-0 (4-bromophenyl)(thien-2-yl)methanone 

Relevant academic research and scientific papers

Photocatalysis and self-catalyzed photobleaching with covalently-linked chromophore-quencher conjugates built around BOPHY

Two Chromophore-Quencher Conjugates (CQCs) have been synthesized by covalent attachment of the anti-oxidant dibutylated-hydroxytoluene (BHT) to a pyrrole-BF2 chromophore (BOPHY) in an effort to protect the latter against photofading. In fluid s

Photocatalytic aldehydes/alcohols/toluenes oxidative amidation over bifunctional Pd/MOFs: Effect of Fe-O clusters and Lewis acid sites

Heterogeneous photocatalytic organic synthesis is fascinating because of the utilization of ubiquitous solar light for chemical transformations. Here, three Fe-MOFs with different Fe-O clusters, Lewis acid sites and morphologies were synthesized through coordination structure engineering. Pd/Fe-MOFs nanocomposites were used to challenge the amide bond green synthesis with visible light. Pd/MIL-101(Fe) exhibited the best photocatalytic performance due to the easily excited Fe3-μ3-oxo clusters for light absorption, the efficient photogenerated carriers separation and migration, the large amount of Lewis acid sites based aldehydes and amines condensation promotion and the efficient O2 reduction to superoxide radicals over photogenerated electron-rich Pd NPs. Various aldehydes, alcohols and toluenes could be transformed to amide compounds with amines over Pd/MIL-101(Fe) with just oxygen or air as the green oxidant and water as the by-product. One-pot C–C cross-coupling and photo-redox C–N coupling cascade reactions could also be achieved over Pd/MIL-101(Fe). This work shed light on the efficient and sustainable amide bonds synthesis.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Cobalt(iii)-catalyzed C-H amidation of: N, N -dialkyl thiobenzamides by sulfur coordination

An efficient inexpensive cobalt(iii)-catalyzed intermolecular amidation of N,N-dialkyl thiobenzamides with 1,4,2-dioxazol-5-ones via C-H bond activation is described. The reaction proceeds with high functional group tolerance under external oxidant free conditions, providing a straightforward approach for the direct modification of thioamide derivatives, which are prevalent organic motifs found in vital biological and pharmaceutical molecules. This journal is

Visible-Light-Mediated Oxidative Amidation of Aldehydes by Using Magnetic CdS Quantum Dots as a Photocatalyst

A magnetic CdS quantum dot (Fe3O4/polydopamine (PDA)/CdS) was synthesized through a facile and convenient method from inexpensive starting materials. Characterization of the prepared catalyst was performed by means of FTIR spectrosco

Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.

NaI-mediated oxidative amidation of benzyl alcohols/aromatic aldehydes to benzamides via electrochemical reaction

In this research, we have developed a mild electrochemical process for oxidative amidation of benzyl alcohols/aromatic aldehydes with cyclic amines into the corresponding benzamides. This electroorganic synthetic method proceeds using NaI as a redox mediator under ambient temperature in undivided cell, providing more than 25 examples of amide products in moderate to good yields. The benefits of this reaction include one-pot synthesis, open air condition, proceed in aqueous media and no requirement of external conducting salt, base and oxidant.

Visible-Light-Driven C-N Bond Formation by a Hexanickel Cluster Substituted Polyoxometalate-Based Photocatalyst

A powerful and attractive route to develop novel photocatalysts for C-N bond formation involves the use of pyrrolidine as the substrate and cocatalyst simultaneously. Herein, a new polyoxometalate (POM)-based metal-organic framework, namely, [Ni6(OH)3(H2O

UV-Light-Induced N-Acylation of Amines with α-Diketones

Herein, we develop a mild method for N-acylation of primary and secondary amines with α-diketones induced by ultraviolet (UV) light. Forty-six examples with various functional groups are explored at room temperature with irradiation by three 26 W UV lamps (350-380 nm). The yield reaches 97%. The gram scale experiment product yield is 76%. Moreover, this system can be applied to the synthesis of several amino acid derivatives. Mechanistic studies show that benzoin is generated in situ from benzil under UV irradiation.

Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF

We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.